Literature DB >> 20023913

Gadolinium texaphyrin (Gd-Tex)-malonato-platinum conjugates: synthesis and comparison with carboplatin in normal and Pt-resistant cell lines.

Jonathan F Arambula1, Jonathan L Sessler, Mark E Fountain, Wen-hao Wei, Darren Magda, Zahid H Siddik.   

Abstract

The synthesis of a new PEG-solubilized n class="Chemical">gadolinium texaphyrin (Gd-Tex) conjugate containing a malonate-Pt(NH(3))(2) moiety is described. The effect of the tumor localizing Gd-Tex macrocycle on platinum activity was evaluated in cell culture. The malonate moiety, analogous to that present in carboplatin, is expected to release an aquated Pt(NH(3))(2) species under physiological conditions. The half-life in phosphate-buffered saline was found to be ca. 3 days at room temperature, and the hydrolytic product released from the conjugate was collected and confirmed as Pt-based by flameless atomic absorption spectrophotometry. Anti-proliferative activity was tested using A549 human lung cancer and A2780 human ovarian cancer cell lines. In both cell lines, the activity of the Gd-Tex conjugate was found to be similar to that of carboplatin. Efficacy against a Pt-resistant ovarian cell line greater than that displayed by carboplatin was also observed.

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Year:  2009        PMID: 20023913      PMCID: PMC2862451          DOI: 10.1039/b912089k

Source DB:  PubMed          Journal:  Dalton Trans        ISSN: 1477-9226            Impact factor:   4.390


  27 in total

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2.  Gadolinium(III) texaphyrin: a tumor selective radiation sensitizer that is detectable by MRI.

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Journal:  Proc Natl Acad Sci U S A       Date:  1996-06-25       Impact factor: 11.205

Review 3.  Cisplatin and derived anticancer drugs: mechanism and current status of DNA binding.

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4.  In vivo animal studies with gadolinium (III) texaphyrin as a radiation enhancer.

Authors:  R A Miller; K Woodburn; Q Fan; M F Renschler; J L Sessler; J A Koutcher
Journal:  Int J Radiat Oncol Biol Phys       Date:  1999-11-01       Impact factor: 7.038

5.  Preclinical evaluation of gadolinium (III) texaphyrin complex. A new paramagnetic contrast agent for magnetic resonance imaging.

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Journal:  Invest Radiol       Date:  1994-03       Impact factor: 6.016

6.  Preclinical antitumor evaluation of bis-acetato-ammine-dichloro-cyclohexylamine platinum(IV): an orally active platinum drug.

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Journal:  Cancer Res       Date:  1993-06-01       Impact factor: 12.701

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Authors:  P T Ho; K Ngu
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8.  Axial ligands and alicyclic ring size modulate the activity and biochemical pharmacology of ammine/cycloalkylamine-platinum(IV) complexes in tumor cells resistant to cis-diamminedichloroplatinum(II) or trans-1R,2R-1S,2S-diaminocyclohexanetetrachloroplatinum(IV).

Authors:  M Yoshida; A R Khokhar; Z H Siddik
Journal:  Cancer Res       Date:  1994-09-01       Impact factor: 12.701

9.  A histochemical approach to the mechanism of action of cisplatin and its analogues.

Authors:  S K Aggarwal
Journal:  J Histochem Cytochem       Date:  1993-07       Impact factor: 2.479

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Authors:  D Gibson; K F Gean; R Ben-Shoshan; A Ramu; I Ringel; J Katzhendler
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  7 in total

1.  Bismuth- and lead-texaphyrin complexes: towards potential α-core emitters for radiotherapy.

Authors:  Christian Preihs; Jonathan F Arambula; Vincent M Lynch; Zahid H Siddik; Jonathan L Sessler
Journal:  Chem Commun (Camb)       Date:  2010-10-04       Impact factor: 6.222

Review 2.  Texaphyrins: tumor localizing redox active expanded porphyrins.

Authors:  Jonathan F Arambula; Christian Preihs; Derric Borthwick; Darren Magda; Jonathan L Sessler
Journal:  Anticancer Agents Med Chem       Date:  2011-02       Impact factor: 2.505

3.  Overcoming biochemical pharmacologic mechanisms of platinum resistance with a texaphyrin-platinum conjugate.

Authors:  Jonathan F Arambula; Jonathan L Sessler; Zahid H Siddik
Journal:  Bioorg Med Chem Lett       Date:  2011-01-26       Impact factor: 2.823

4.  Porphyrinoid Drug Conjugates.

Authors:  Jonathan F Arambula; Jonathan L Sessler
Journal:  Chem       Date:  2020-07-09       Impact factor: 22.804

5.  Oxaliplatin Pt(IV) prodrugs conjugated to gadolinium-texaphyrin as potential antitumor agents.

Authors:  Grégory Thiabaud; Guangan He; Sajal Sen; Kathryn A Shelton; Wallace B Baze; Luke Segura; Julie Alaniz; Ruben Munoz Macias; Greg Lyness; Alan B Watts; Hyun Min Kim; Hyunseung Lee; Mi Young Cho; Kwan Soo Hong; Rick Finch; Zahid H Siddik; Jonathan F Arambula; Jonathan L Sessler
Journal:  Proc Natl Acad Sci U S A       Date:  2020-03-16       Impact factor: 11.205

Review 6.  Recent developments in texaphyrin chemistry and drug discovery.

Authors:  Christian Preihs; Jonathan F Arambula; Darren Magda; Heeyeong Jeong; Dongwon Yoo; Jinwoo Cheon; Zahid H Siddik; Jonathan L Sessler
Journal:  Inorg Chem       Date:  2013-04-04       Impact factor: 5.165

7.  A texaphyrin-oxaliplatin conjugate that overcomes both pharmacologic and molecular mechanisms of cisplatin resistance in cancer cells.

Authors:  Jonathan F Arambula; Jonathan L Sessler; Zahid H Siddik
Journal:  Medchemcomm       Date:  2012       Impact factor: 3.597

  7 in total

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